What is a Short-term vacation rental?

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In most Non-Deed Restricted areas of Sarasota county, short term rentals are allowed and well reciprocated. However, there is a seven day MINIMUM on all rentals. Weekly (short-term) rentals are thriving all over Sarasota. Tourists are flocking down and looking for unique places to stay near the beach. Short term rentals are in demand, all year round, and ownership promises an impressive immediate return on investment. These properties command increasing rental rates, more in-line with hotels, along with appreciating Sarasota Real Estate values. The outstanding cash-flow generated by weekly rentals, when managed by Pink Pineapple, make this a unique investment opportunity. We will help you understand what to project for rate of return on your short-term rental investment.

Having a successful rental property requires a lot of time, effort, experience and knowledge. Let us save you the time and frustration that comes with gaining this experience. We pride ourselves on serving the guest by providing a sparkling clean, beautifully curated space for them to call home while they enjoy everything that Sarasota has to offer.  We also offer concierge service to guests that includes grocery shopping, car rental, and other amazing perks! Our properties are booked 95% of the year and get 5-star ratings every time. 

A la Carte Services

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Outfitting the property with the essentials

Plates, silverware, toilet paper, hand soap, towels, etc.…Preparing a house to become a vacation rental can be exhausting and expensive!  Savvy travelers expect certain amenities and are attracted to colors and styles that give them a feeling of cleanliness and have a high-end feel. Let us handle the set up by providing the essential goods you need to host your first guest by tapping into our carefully sourced (and tested) companies. These are not just the essentials; they are the products that make the difference between a 4-star guest and a 5-start ecstatic repeat client. We will check every box and ensure your guest will be provided with everything they need for an enjoyable stay.

Vacation Rental Design

When decorating a vacation rental, we use the techniques I perfected during my staging career. I am inspired by the demographics of the potential guests and easily visualize and curate the property to appeal to a large pool of potential guests. A vacation rental in Sarasota should have a fun yet sophisticated vibe that provides a nod to the beach without being “beach themed”. We accomplish this through our use of colors, textures, artwork and unique accessories.

listing Photography

The most important factor for luring in the perfect guest is the photos! Professional photography goes hand in hand with incredible décor. We provide the highest quality photography so that the guest knows exactly what the property looks like prior to walking in the door. We want the guest to be excited about booking your home and share their excitement with social media by posting photos and links to the house they get to live in while on vacation! The guest is taking pride in the property and will treat it with respect while vacationing.

compelling listings

The way your listing is described and marketed on any rental platform is important for securing quality guests. People will not click the “Info” button unless they are excited about the pictures of the space. This is your chance to really connect with the guest emotionally. This is where we tell a story about their perfect vacation and help them imagine savoring an ice-cold cocktail on the oversized screened lanai, cooling off in the incredible lap pool, or enjoying a lazy day relaxing on the cloud-like king bed.  Once the guest has pictured themselves living this lifestyle, they are ready to book!

booking & payments

Once your property is listed, we manage the calendar/bookings, communicate with guests, answer questions and keep the listing fresh by adding new pictures and revamping content when needed. Because we are already SUPER HOSTS, your property will immediately have Super Host status. That means that it will be seen before properties that are not managed by super hosts and it is more likely to be booked because people feel more confident booking with a Super Host!

Hospitality Management

From the moment the guest inquiries about the property they are treated as family. We answer any questions they have prior to booking and once they book each guest has access to our personal email and cell phone numbers. Our hospitality and concierge services shine through from day one. We want to make their trip effortless and provide many add-ons that help ease the stress of planning. During their stay, we communicate with intelligence and enthusiasm. This translates into confidence—guests know when they pick up the phone they are in capable hands 24/7.


Cleanliness is the cornerstone of overall guest satisfaction. We maintain your home as if it were our own. Our “Safe Space Certified” Housekeeping partner has received training in the proper sanitization and disinfection practices and procedures consistent with the current highest industry standards. They will arrive immediately upon guest departure to clean your property as well as to refresh and restock linens, sheets, towels and essentials. The bathrooms are furnished with complimentary toiletries to ensure guests have everything they need to optimize their stay. We also conduct a thorough evaluation of the property prior to the next guest checking in.


We are a family business and find it beneficial to work with other local family businesses. We uphold strong working relationships with several local contractors and venders to ensure quick and thorough work.  We pride ourselves on clear, open communication with our owners, and solve maintenance issues with common sense solutions. Our on-staff handyman can complete most tasks within a few hours to ensure the guests have the best vacation possible.